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Process for preparing ceftaroline salts or hydrates thereof

Inactive Publication Date: 2014-11-27
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to a process for preparing ceftaroline salts or hydrates thereof. The process involves treating a compound of Formula III or an ester derivative or salt thereof with a compound of Formula IV or a salt or reactive derivative thereof to obtain a reaction mass. The reaction mass is then treated with a salt-forming agent to obtain the ceftaroline salt or hydrate thereof. The technical effect of the invention is a simplified process for the preparation of ceftaroline salts or hydrates thereof, leading to improved efficiency and lower costs of production.

Problems solved by technology

The steps of chromatographic elution and lyophilization make the processes of Japan Patent No. 3927262 B2 and U.S. Pat. No. 6,417,175 unsuitable at an industrial scale.
Further, Japan Patent No. 3927262 B2 and U.S. Pat. No. 6,417,175 do not provide a method of preparing ceftaroline salts.
Further, the process provided in the Japan Patent No. 4656798 B2 does not disclose purity of ceftaroline hydrochloride.
The Japan Patent No. 4656798 B2 discloses that ceftaroline has stability and quality control problems.
The preparation of ceftaroline fosamil or its acetic acid solvate, followed by its conversion into ceftaroline hydrochloride or hydrates thereof, increases the number of steps and makes the process costly.

Method used

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  • Process for preparing ceftaroline salts or hydrates thereof
  • Process for preparing ceftaroline salts or hydrates thereof
  • Process for preparing ceftaroline salts or hydrates thereof

Examples

Experimental program
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Effect test

example 1

Preparation of S-1,3-Benzothiazol-2-Y1(2z)-(5-Amino-1,2,4-Thiadiazol-3-Y1)(Ethoxyimino)Ethanethioate (Reactive Derivative of Formula IV)

[0046]Triphenylphosphine (16 g, 0.06 moles) and (2Z)-(5-amino-1,2,4-thiadiazol-3-yl)(ethoxyimino)ethanoic acid (Formula IV; 10 g, 0.046 moles) were treated in dichloromethane (60 mL) at 25° C. to 30° C. The resulting reaction mass was stirred for 1 to 2 hours at 25° C. to 30° C. and then cooled to 0° C. 2,2′-Disulfanediylbis(1,3-benzothiazole) (20.2 g, 0.06 moles) was added to the reaction mass at 0° C. to 5° C. Triethylamine (5.14 g, 0.051 moles) was added drop wise to the reaction mass over 5 to 10 minutes at 0° C. to 5° C. The resulting reaction mass was stirred for 3 to 4 hours at 0° C. to 5° C. and was allowed to stand for 1 to 4 hours. The solid obtained was filtered, washed with dichloromethane, and dried in an air oven for 10 to 12 hours at 40° C. to 45° C. Yield=22.2 g (88% yield)

example 2

Preparation of Ceftaroline Dihydrochloride (Formula IIa)

[0047]7-Amino-3-{[4-(1-methyl pyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1l-aza bicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride (hydrochloride salt of Formula III; 10 g, 0.0208 moles) and S-1,3-benzothiazol-2-yl(2Z)-(5-amino-1,2,4-thiadiazol-3-yl)(ethoxyimino)ethanethioate (reactive derivative of Formula IV; 22.2 g, 0.042 moles) were treated in a mixture of tetrahydrofuran and water (3:2; 200 mL) at 25° C. to 30° C. Tributylamine (10.7 g, 0.0581 moles) was added in 10 minutes and the resulting mass was stirred for 3 to 5 hours at 30° C. to 35° C. Ethyl acetate (100 mL) was added to the resulting mass. It was stirred and the aqueous layer was separated. Ethanol (150 mL) and hydrochloric acid (35%; 30 mL) were added to the aqueous layer at 15° C. to 20° C. and the resulting mass was stirred for 10 to 12 hours at 15° C. to 20° C. The solid obtained was filtered, washed with ethanol, and dried under vacuum for 10 ...

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Abstract

The present invention relates to a process for the preparation of ceftaroline salts or hydrates thereof.

Description

FIELD OF THE INVENTION[0001]The present invention relates to a process for the preparation of ceftaroline salts or hydrates thereof.BACKGROUND OF THE INVENTION[0002]Ceftaroline fosamil is chemically known as (6,7)-7-{(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetamido}-3-{[4-(1-methyl pyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate monoacetate monohydrate, of Formula I.[0003]Ceftaroline fosamil is a phosphate prodrug of ceftaroline of Formula II and is indicated for the treatment of acute bacterial skin and skin structure infections and community-acquired bacterial pneumonia.[0004]Japan Patent No. 3927262 B2 provides a process for the preparation of ceftaroline, wherein 7-amino-3-[4-(1-methylpyridinium-4-yl)thiazol-2-yl]thio-3-cephem-4-carboxylate is dissolved in a water-tetrahydrofuran mixture (1:2) in the presence of aqueous sodium bicarbonate. This solution is treated with 2-(5-amino-1,2,4-thiadiazol-3-...

Claims

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Application Information

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IPC IPC(8): C07D501/06
CPCC07D501/06
Inventor MOHAMMAD, KALLIMULLARAI, BISHWA PRAKASHTEWARI, NEERA
Owner RANBAXY LAB LTD
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